Androstadienone

Androstadienone, or androsta-4,16-dien-3-one, is a 16-androstene class endogenous steroid that has been described as having potent pheromone-like activities in humans.^[1] The compound is synthesized from androstadienol by 3β-hydroxysteroid dehydrogenase, and can be converted into androstenone (a more potent and odorous pheromone) by 5α-reductase, which can subsequently be converted into 3α-androstenol or 3β-androstenol (also more potent and odorous pheromones) by 3-ketosteroid reductase.^[2]

Androstadienone

Clinical data
ATC code	none
Identifiers
IUPAC name (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
CAS Number	4075-07-4 Y
PubChem CID	92979
ChemSpider	83932 Y
UNII	ZUZ4FHD36E
CompTox Dashboard (EPA)	DTXSID00863314
Chemical and physical data
Formula	C19H26O
Molar mass	270.416 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C
InChI InChI=1S/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3/t15-,16-,17-,18-,19-/m0/s1 Y Key:HNDHDMOSWUAEAW-VMXHOPILSA-N Y
NY (what is this?)  (verify)

Androstadienone is related to the androgen sex hormones; however, androstadienone does not exhibit any androgenic or anabolic effects. Though it has been reported to significantly affect the mood of heterosexual women and homosexual men, it does not alter behavior overtly,^[3][4][5][6] although it may have more subtle effects on attention.^[7]

Androstadienone is commonly sold in male fragrances; it is purported to increase sexual attraction. Androstadienone, in picogram quantities, has been shown to have "significant reduction of nervousness, tension and other negative feeling states" in female subjects.^[8]

See also

• List of neurosteroids § Pheromones and pherines